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Winchester Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
47 rentals in Winchester.
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, vacation rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, vacation rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, vacation rental in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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House on A+ school area w/AC & W/D, vacation rental in Winchester
House on A+ school area w/AC & W/D, vacation rental in Winchester
House on A+ school area w/AC & W/D, vacation rental in Winchester

House on A+ school area w/AC & W/D

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The following properties within 20 miles of Winchester match all your filters:
Beautiful renovated 3 bedroom apt near Boston., vacation rental in Winchester
Beautiful renovated 3 bedroom apt near Boston., vacation rental in Winchester
Beautiful renovated 3 bedroom apt near Boston., vacation rental in Winchester

Beautiful renovated 3 bedroom apt near Boston.

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., vacation rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., vacation rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., vacation rental in Winchester

Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amsden Place, vacation rental in Winchester
Amsden Place, vacation rental in Winchester
Amsden Place, vacation rental in Winchester

Amsden Place

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A charming modern suburban 3 bedroom condo close to Boston, vacation rental in Winchester
A charming modern suburban 3 bedroom condo close to Boston, vacation rental in Winchester
A charming modern suburban 3 bedroom condo close to Boston, vacation rental in Winchester

A charming modern suburban 3 bedroom condo close to Boston

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Stoneham Getaway Just Minutes to Boston!, vacation rental in Winchester
Perfect Stoneham Getaway Just Minutes to Boston!, vacation rental in Winchester
Perfect Stoneham Getaway Just Minutes to Boston!, vacation rental in Winchester

Perfect Stoneham Getaway Just Minutes to Boston!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 1 BR private entrance apt commuters dream, vacation rental in Winchester
Charming 1 BR private entrance apt commuters dream, vacation rental in Winchester
Charming 1 BR private entrance apt commuters dream, vacation rental in Winchester

Charming 1 BR private entrance apt commuters dream

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unique loft style garden level studio apartment, vacation rental in Winchester
Unique loft style garden level studio apartment, vacation rental in Winchester
Unique loft style garden level studio apartment, vacation rental in Winchester

Unique loft style garden level studio apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cheerful 1-bedroom New England Ranch, vacation rental in Winchester
Cheerful 1-bedroom New England Ranch, vacation rental in Winchester
Cheerful 1-bedroom New England Ranch, vacation rental in Winchester

Cheerful 1-bedroom New England Ranch

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Located north of Boston/ comfort and relaxation in your home away from home, vacation rental in Winchester
Located north of Boston/ comfort and relaxation in your home away from home, vacation rental in Winchester
Located north of Boston/ comfort and relaxation in your home away from home, vacation rental in Winchester

Located north of Boston/ comfort and relaxation in your home away from home

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 2 bedroom Medford, vacation rental in Winchester
Cozy 2 bedroom Medford, vacation rental in Winchester
Cozy 2 bedroom Medford, vacation rental in Winchester

Cozy 2 bedroom Medford

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Colonial Two Bedroom Basement Apartment, vacation rental in Winchester
Charming Colonial Two Bedroom Basement Apartment, vacation rental in Winchester
Charming Colonial Two Bedroom Basement Apartment, vacation rental in Winchester

Charming Colonial Two Bedroom Basement Apartment

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakeview Oasis in Arlington 15 Minutes to Downtown Boston, vacation rental in Winchester
Lakeview Oasis in Arlington 15 Minutes to Downtown Boston, vacation rental in Winchester
Lakeview Oasis in Arlington 15 Minutes to Downtown Boston, vacation rental in Winchester

Lakeview Oasis in Arlington 15 Minutes to Downtown Boston

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Melrose two bedroomer, vacation rental in Winchester
Melrose two bedroomer, vacation rental in Winchester
Melrose two bedroomer, vacation rental in Winchester

Melrose two bedroomer

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet Family Neighborhood, vacation rental in Winchester
Quiet Family Neighborhood, vacation rental in Winchester
Quiet Family Neighborhood, vacation rental in Winchester

Quiet Family Neighborhood

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hot Tub Retreat, vacation rental in Winchester
Hot Tub Retreat, vacation rental in Winchester
Hot Tub Retreat, vacation rental in Winchester

Hot Tub Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Clean apartment - 5 miles from Boston, vacation rental in Winchester
Clean apartment - 5 miles from Boston, vacation rental in Winchester
Clean apartment - 5 miles from Boston, vacation rental in Winchester

Clean apartment - 5 miles from Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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★Modern Studio-Private Entrance,Washer+Dryer★, vacation rental in Winchester
★Modern Studio-Private Entrance,Washer+Dryer★, vacation rental in Winchester
★Modern Studio-Private Entrance,Washer+Dryer★, vacation rental in Winchester

★Modern Studio-Private Entrance,Washer+Dryer★

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Downtown Woburn Rental w/ Walkable Location!, vacation rental in Winchester
Cozy Downtown Woburn Rental w/ Walkable Location!, vacation rental in Winchester
Cozy Downtown Woburn Rental w/ Walkable Location!, vacation rental in Winchester

Cozy Downtown Woburn Rental w/ Walkable Location!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amsden Place (*Tufts, Harvard, MIT), vacation rental in Winchester
Amsden Place (*Tufts, Harvard, MIT), vacation rental in Winchester
Amsden Place (*Tufts, Harvard, MIT), vacation rental in Winchester

Amsden Place (*Tufts, Harvard, MIT)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful 2beds/1bath w/free parking & 10mnts away from Boston, vacation rental in Winchester
Beautiful 2beds/1bath w/free parking & 10mnts away from Boston, vacation rental in Winchester
Beautiful 2beds/1bath w/free parking & 10mnts away from Boston, vacation rental in Winchester

Beautiful 2beds/1bath w/free parking & 10mnts away from Boston

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Stylish Studio - ✓Sanitized ✓Private ✓Spotless, vacation rental in Winchester
Stylish Studio - ✓Sanitized ✓Private ✓Spotless, vacation rental in Winchester
Stylish Studio - ✓Sanitized ✓Private ✓Spotless, vacation rental in Winchester

Stylish Studio - ✓Sanitized ✓Private ✓Spotless

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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♥ Lovely Studio - Spotless, W/D, Parking, Private, vacation rental in Winchester
♥ Lovely Studio - Spotless, W/D, Parking, Private, vacation rental in Winchester
♥ Lovely Studio - Spotless, W/D, Parking, Private, vacation rental in Winchester

♥ Lovely Studio - Spotless, W/D, Parking, Private

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, vacation rental in Winchester
Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, vacation rental in Winchester
Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, vacation rental in Winchester

Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 2 bedroom Townhome w/private office suite, vacation rental in Winchester
Charming 2 bedroom Townhome w/private office suite, vacation rental in Winchester
Charming 2 bedroom Townhome w/private office suite, vacation rental in Winchester

Charming 2 bedroom Townhome w/private office suite

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, vacation rental in Winchester
Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, vacation rental in Winchester
Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, vacation rental in Winchester

Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Modern Two Bedroom Condo - Near Boston, vacation rental in Winchester
Modern Two Bedroom Condo - Near Boston, vacation rental in Winchester
Modern Two Bedroom Condo - Near Boston, vacation rental in Winchester

Modern Two Bedroom Condo - Near Boston

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, vacation rental in Winchester
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, vacation rental in Winchester
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, vacation rental in Winchester

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Malden West End Apartment close to Boston, vacation rental in Winchester
Malden West End Apartment close to Boston, vacation rental in Winchester
Malden West End Apartment close to Boston, vacation rental in Winchester

Malden West End Apartment close to Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Unique Cathedral Ceiling Condo W/D, Parking, vacation rental in Winchester
Unique Cathedral Ceiling Condo W/D, Parking, vacation rental in Winchester
Unique Cathedral Ceiling Condo W/D, Parking, vacation rental in Winchester

Unique Cathedral Ceiling Condo W/D, Parking

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Vibrant and Welcoming Cozy Home for your visit to Boston!, vacation rental in Winchester
A Vibrant and Welcoming Cozy Home for your visit to Boston!, vacation rental in Winchester
A Vibrant and Welcoming Cozy Home for your visit to Boston!, vacation rental in Winchester

A Vibrant and Welcoming Cozy Home for your visit to Boston!

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home away from home for work or graduate school., vacation rental in Winchester
Home away from home for work or graduate school., vacation rental in Winchester
Home away from home for work or graduate school., vacation rental in Winchester

Home away from home for work or graduate school.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quiet and spacious 2 floor-3 bedroom condo, vacation rental in Winchester
Quiet and spacious 2 floor-3 bedroom condo, vacation rental in Winchester
Quiet and spacious 2 floor-3 bedroom condo, vacation rental in Winchester

Quiet and spacious 2 floor-3 bedroom condo

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Apartment - 5 miles from Boston!, vacation rental in Winchester
Spacious Apartment - 5 miles from Boston!, vacation rental in Winchester
Spacious Apartment - 5 miles from Boston!, vacation rental in Winchester

Spacious Apartment - 5 miles from Boston!

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sphisticated, bright, and cheerful 2 story home, vacation rental in Winchester
Sphisticated, bright, and cheerful 2 story home, vacation rental in Winchester
Sphisticated, bright, and cheerful 2 story home, vacation rental in Winchester

Sphisticated, bright, and cheerful 2 story home

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, vacation rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, vacation rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, vacation rental in Winchester

Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern Three Bedroom Condo - Near Boston, vacation rental in Winchester
Modern Three Bedroom Condo - Near Boston, vacation rental in Winchester
Modern Three Bedroom Condo - Near Boston, vacation rental in Winchester

Modern Three Bedroom Condo - Near Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Designer Style 3Br, King Bed, W/D,Parking,Spotless, vacation rental in Winchester
Designer Style 3Br, King Bed, W/D,Parking,Spotless, vacation rental in Winchester
Designer Style 3Br, King Bed, W/D,Parking,Spotless, vacation rental in Winchester

Designer Style 3Br, King Bed, W/D,Parking,Spotless

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, vacation rental in Winchester
Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, vacation rental in Winchester
Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, vacation rental in Winchester

Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Deluxe and Bright 3Br, King Bed,W/D,Parking, vacation rental in Winchester
Deluxe and Bright 3Br, King Bed,W/D,Parking, vacation rental in Winchester
Deluxe and Bright 3Br, King Bed,W/D,Parking, vacation rental in Winchester

Deluxe and Bright 3Br, King Bed,W/D,Parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Boston area house & gardens, near parks, farms, woods trails, shops, buses, vacation rental in Winchester
Boston area house & gardens, near parks, farms, woods trails, shops, buses, vacation rental in Winchester
Boston area house & gardens, near parks, farms, woods trails, shops, buses, vacation rental in Winchester

Boston area house & gardens, near parks, farms, woods trails, shops, buses

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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10 Minute drive to Boston - 3 Bedrooms, 2 full baths, 1 half., vacation rental in Winchester
10 Minute drive to Boston - 3 Bedrooms, 2 full baths, 1 half., vacation rental in Winchester
10 Minute drive to Boston - 3 Bedrooms, 2 full baths, 1 half., vacation rental in Winchester

10 Minute drive to Boston - 3 Bedrooms, 2 full baths, 1 half.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Home in Woburn - Family + Pet Friendly!, vacation rental in Winchester
Home in Woburn - Family + Pet Friendly!, vacation rental in Winchester
Home in Woburn - Family + Pet Friendly!, vacation rental in Winchester

Home in Woburn - Family + Pet Friendly!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, vacation rental in Winchester
Beautiful, vacation rental in Winchester
Beautiful, vacation rental in Winchester

Beautiful

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Single Family  with Central AC, vacation rental in Winchester
New Single Family  with Central AC, vacation rental in Winchester
New Single Family  with Central AC, vacation rental in Winchester

New Single Family with Central AC

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, vacation rental in Winchester
Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, vacation rental in Winchester
Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, vacation rental in Winchester

Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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